The boy in the front row

used drawing paddle hold (5)

I am quite alone. The door is locked from the outside, it will not be opened until morning. Soon the light will go out, plunging me into darkness. My eyes are awash, but tears are not yet falling. Someone seems to have put my temples in a vice.

Let me try to explain what is happening. I am (sorry, I was) the headmaster of C_______________ College, the most upscale school in this part of the world. You will have heard of it; old money and tradition.

I first saw John in my English class. He is eighteen years old and a new boy. That is not unusual. We often take brilliant young scholars for a year and prepare them for a top university. John aced every test there was in his state. He is destined for great things.

It happened in the third class of the semester. John always sits at the front of the room. He reads voraciously and answers my questions with a confidence belying his years. He has his hair cut military style but has an unusual habit of running his fingers across his scalp as if he had long, flowing locks. Perhaps his crew cut is recent; a new look to go with his new life at school.

He has the most piercing green eyes I have ever encountered. They sparkle when he thinks. They are set symmetrically either side of a button nose, which hovers above slightly crooked lips. When he smiles he exposes uneven teeth. They are not tombstones, but they reflect his family’s lower income status. John is most certainly a scholarship boy.

What is it about those damn eyes? They began to haunt me. Almost literally. I dreamed of the boy night after night. As I recall nothing much happened, but he was constantly in my thoughts, beguiling me. I have a drink problem – there I confess it – but it wasn’t the wine that drove me forward. Indeed, most unusually for me, I had not touched alcohol all day.

Don’t ask me why I did it, I still don’t know the answer to that. I could have understood it had I been rip-roaring drunk. I had asked my secretary Mrs. Crabbe to bring me Mr. McAlpine’s file – we are always so formal when referring to our students. I found the number of his room at the boys’ dormitory and set off just before lights out. My wife has already gone to her bed in her own room. When did we start sleeping apart? I can’t be certain; sometime after our only son went off to the war, I think.

It is quite a trek from the headmaster’s house, through the quadrangle, and across the playing fields to the outlying buildings that comprise the dormitories. Boys and girls are kept separate, of course. It is not usual for the headmaster to visit the boys’ dormitories, but not entirely unheard of. Mr. Albertson, the dorm master, seemed a little flustered when he saw me approaching the building, suspicious perhaps that I had come to spy on him. I don’t know what goes on in the boys’ dorms at night and it would probably be injudicious to inquire.

John’s room was on the third floor at the far end of a corridor. His door was ajar and he was alone. He lay on his bed reading a book. He wore only khaki shorts, adding to his general military appearance. He looked up from his book as if he had been expecting me.  He smiled, those eyes dancing. Quietly, I closed the door behind me.

John is short for his age, I think. Maybe five-seven or so. His waist is narrow and his chest broad. I suspect he uses the gym. His torso is hairless, but a fine down covers his legs. He wriggled to a seating position and reached over and set his book down on the nightstand. It was then that I noticed the whisky bottle. My, how I wanted to grab it and glug down its contents. John saw that I had spied the bottle. His crooked lips parted.

It is against the rules for students to have alcohol. The penalty is strict: expulsion. John knew that, but I reminded him all the same.

He ran his fingers through his almost non-existent hair. I watched the muscles on his arms tense. He gazed at me. “Oh,” he said, “Couldn’t you just paddle me instead.” My jaw must have dropped, or at least I gaped disbelief.

“Paddle me.”

I cannot explain what happened next. That is, I can describe what happened, but I am still unsure why it happened. I am the headmaster of C_______________ College, I am fifty-five years old and have been around young men my whole life and have never given their bodies a passing consideration. I pull him toward me awkwardly, clumsily, unannounced. I am about to do something that will change my life forever. It will in all inevitability be my ruin. He is in my arms and I kiss him forcefully on the mouth.

But, John does not retreat from me; he kisses me back. Passionately. My hands run across his scalp, it feels like petting a hedgehog. Our teeth meet, tongues grope for each other. I run my hand over his warm, smooth naked flesh. My erection presses against the front of my underpants.

Then the lights go out and we plunge into darkness. The boys’ dorm can be like a prison. It is ten-thirty and all must be in bed. John gently pushes me away. I must leave. It would be unseemly for the headmaster to be caught in the dark in the bedroom of an eighteen-year-old male student.

I fumble for the door and as I leave I whisper, “My study, after school tomorrow evening.” It is a rendezvous with the paddle.

We haven’t used corporal punishment at the college since my father was headmaster. He was a devotee of the paddle, but once he retired it fell into disuse. Times, I suppose, have changed. The boys in the athletics clubs continue to use it. I believe the rowers especially paddle each other’s rear ends when they lose a race, which, now I come to think of it, is very often.

We still have my father’s paddles in storage and it is no problem for me to blow the dust off one of them. I have a fretful day. The college governors are in town and I am forced to sit through interminable committee meetings when all I want to do was stroll through the campus in the hope of catching a glimpse of my beloved John.

At last, the afternoon draws to a close. Mrs. Crabbe is tidying her desk when he arrives. She passes me a quizzical look, when she announces Mr. McAlpine is here to see me. Mrs. Crabbe keeps my diary and nobody, not even the chairman of the governors himself, gets to see me without her say-so. Why do I feel like a naughty boy found out in some misdeed? I croak that she should leave; her services are no longer needed.

I wait until from my study window I see Mrs. Crabbe pass through the quadrangle and then I order John into my study. It is a huge room befitting a man of my status at the school. At one end is my desk and cupboards for my official paperwork. At the far end are leather armchairs, a small table and bookcases. I order John to stand close to a chair. He does so without a murmur.

He is dressed in a blue jacket and cream chinos which passes for the school uniform here. His white shirt is immaculate and a wine-coloured tie is tightly knotted at his neck. His face shines. I imagine he is having second thoughts. But, it is his idea to be here. He could face expulsion and disgrace. I am sure his impoverished parents are extremely proud of him. They would die of shame.

I had placed the paddle in a drawer. I didn’t want it to attract attention, not with Mrs. Crabbe snooping around. I remind John of why we are here. He chews his bottom lip. My heart skips a beat. I want to pull him towards me and put my tongue down his throat. Instead, calmly I open the drawer and pull out the paddle. John’s eyes widen.

And, so they might. It is an awesome specimen. It is more than two feet in length and maybe four wide. Large holes have been drilled into the blade to reduce wind resistance during the swing. John appears to be sweating. His eyes follow my movements when I hold the paddle by its handle and smack the blade into my left palm. I have never spanked a boy before, but I know that this wood is capable of inflicting great pain.

“Take off your jacket, put it on the table,” I have decided he should put himself across the back of one of the leather armchairs. It is low and his buttocks will be presented perfectly. He slips the coat from his shoulders and folds it neatly on the table. The tail of his shirt is poking out of his chinos. I see they fit him tightly at the waist and a fold of cotton covers his buttocks snugly, separating each cheek.

I tap the paddle against the back of the chair. “Bend over.” I say this calmly although my heart is racing and my palms sweat. He gazes at me with those intense green eyes. I flinch a little. Then he does something truly remarkable. He moves into position behind the chair, unfastens his trousers and sends them to his ankles. He is wearing sparkling white boxer shorts. His fingers pinch the cloth at his hips and with the merest flick of the wrists he sends them south to meet his chinos. He swallows hard and bends over.

I have never seen a man’s bare arse so close. His cheeks are smooth and as bald as his torso. His ballsack dangles and I see it too is hairless. His flesh tautens as he stretches over the leather chair. He keeps his head low and his legs apart. I feel that this is not the first time he has submitted himself for a spanking.

I had been dreaming of this moment all day. Except in my version I am paddling the seat of John’s chinos. That in itself is an erotic vision that has my cock tingling. The sight of the eighteen-year-old’s naked buttocks has me hard. I lick my dry lips, take up position a little to John’s left and gently tap-tap-tap the wood against his flesh. His cheeks clench a little. I raise my arm away and bring the paddle down with a resounding crack! I am please Mrs. Crabbe has departed for the day since surely she would have heard the noise and come running.

A dark pink imprint of the blade immediately appears across John’s bottom. It looks sore, but John makes no fuss, his face buried in a cushion. I make another mark, this time on his other buttock. The flesh wobbles. He feels that.

I put the next two swats in the underside of John’s cheeks. His knees buckle and he hangs on to the chair as the pain mounts. I admire the aesthetic effect the paddle has on his once creamy white flesh. By the time I pound home swat number five, some of the pink blotches are turning mauve. The imprint of the blade has been reproduced several times. No square inch of flesh remains untouched.

I appreciate the look of the teenager’s buttocks as increasingly they are battered, but (and I am very nervous to discover this) I also relish the fact that I am hurting him. He squirms with each successive blow and clenches his fists and shuts his teeth. Despite his best efforts he yaps like a dog when I hammer home numbers nine and ten.

I had planned to give him ten swats but I am loving this so much I whack home an additional two.

“Stand up,” I croak, as my mouth is as dry as a desert. I realise the back of my shirt is soaked. My hands are shaking.

John bounds up, his buttocks are sore and so is his cock. It points to the ceiling as he hops from foot to foot and kneads the raw flesh. I find myself staring at his dick and look away fearfully, catching John’s eyes. I think I can read his thoughts. I am on my knees sucking his hairless balls. He spreads his legs and takes hold of the back of my head, urging me on.

“Take it all,” he cries.

Then I have John’s entire shaft in my mouth and throat, squeezing my lips tightly around the base of the eighteen-year-old’s cock.

“Argh, that is so good.’’ John’s fingers dig deep into my scalp. The scratches will be sore for hours.

John gives a low groan, “I’m cumming,” he gasps. I don’t heed the warning. My head continues the  rhythmic up and down motion on John’s rock solid cock. It throbs and I feel spurt after spurt of sticky cum being pumped up his shaft into my hungry mouth.

John pulls away. I don’t see what happens next as I am lying on the floor in the foetal position choking. Should I spit or swallow? I have visions of Mrs. Crabbe’s disapproval as she inspects the stained carpet. That is a humiliation too far; I swallow.

When I look up John has his underwear and chinos back on. He picks up his jacket and without uttering a word, he leaves my study.

I do not see John for three days. The absence is agony. I crave for his body. I need to understand what is going on. He misses my next English class. Is he punishing me? I need to know.

In despair and with half a bottle of whisky inside me, once more I go to his dorm room. He is on the bed wearing the same shorts as before. He looks up from his book as I enter, his look of distain is profound. I mumble incoherently. I am more drunk than I realise. I think I say something about love, or at least lust.

He sneers. Yes, really sneers. He an eighteen-year-old student and me the headmaster of one of the most prestigious schools in the land. But, the humiliation has only just begun.

“It’s a list,” he says, trying to explain what is happening. “Things I want to do once,” he is still lying on the bed but rests on one arm. “Get sucked off by an old man.” His eyes shrug. That is all there is to it, they are saying.

Cry me a river. Tears course down my cheeks. Great sobs rage from my body. The arrogance of the beauty of youth. I stagger forward. I take him by surprise. I roll him so that he is now face down on the bed. He struggles, but even in my drunken stupor I am too strong for him. I dig my knee into his shoulders. He wriggles his hips and waist and flails his legs, but he is going nowhere. Not until I say so.

I tug at the waist of his khaki shorts. He resists but I inch them down over the mounds of his buttocks. His cheeks are bare. I see bruises from the paddling are still to heal completely. I wish I had a paddle. I don’t, so I smack the palm of my hand across his buttocks.

“Gerroff! Leave me alone!” he yells as I pound away at his backside. The flesh feels soft and warm. Soon my palm begins to tingle. It is probably hurting more than John’s rear end. I don’t care. I hate him so much. If I had a knife I would probably plunge it into his heart.

My cock is rock hard. My heart races. My temples throb. I loosen my trousers and find my dick. I climb on his back. John squeals with terror.

“Headmaster, headmaster!” Mr. Albertson, the dorm master, stands in the doorway, ashen-faced. I climb from the bed and without fastening my trousers, I push past him and stagger down the corridor, leaving John convulsing on the bed.

Picture credit: Endart

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The thieving window cleaner

Missed Opportunities

Lord Bowinem’s chauffeur

 

More stories from Charles Hamilton II are on the MMSA website

 

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

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